Sodium Iodide → (S)-N-[3-(benzoylamino)-2-oxo-4-phenylbutyl]-L-alanine, 1,1-dimethylethyl ester

HRID 648830노트

반응식

HRID 648830 반응식
Cl[CH2:2][C:3](=[O:21])[C@@H:4]([NH:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[NH2:23][C@H:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH3:25].C(=O)(O)[O-].[Na+].[I-].[Na+]>CN(C)C=O.CCOCC>[C:13]([NH:12][CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](=[O:21])[CH2:2][NH:23][C@H:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH3:25])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 11275390tert-Butyl alaninate hydrochlorideHCID 13339657(3S)-3-Benzoylamino-1-chloro-4-phenyl-2-butanone

생성물 1

HCID 56609976(S)-N-[3-(benzoylamino)-2-oxo-4-phenylbutyl]-L-alanine, 1,1-dimethylethyl ester

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

To a stirring solution of (S)-N-[3-chloro-2-oxo-1-(phenylmethyl)propyl]benzamide 10.0 g., 33.1 mmole) in dimethylformamide (80 ml.) is added L-alanine, 1,1-dimethylethyl ester, hydrochloride (6.0 g., 33.1 mmole), sodium bicarbonate (6.1 g., 72 mmole) and sodium iodide (4.9 g., 33.1 mmole). The resulting solution is stirred overnight at room temperature, poured into ether and washed with water (twice) and 10% sodium bicarbonate. The ether solution is extracted with 1N hydrochloric acid (3×), the combined extracts are made basic by the addition of solid sodium bicarbonate and extracted with ethyl acetate (4×). The organic extracts are combined, dried (MgSO4) and concentrated to give 8.9 g. of pale yellow solid. A portion of this material is recrystallized from ethyl acetate to give (S)-N-[3-(benzoylamino)-2-oxo-4-phenylbutyl]-L-alanine, 1,1-dimethylethyl ester as a white solid; m.p. 106.5°-110°.

후처리

  1. washwashed with water (twice) and 10% sodium bicarbonate
  2. extractionThe ether solution is extracted with 1N hydrochloric acid (3×)
  3. additionthe combined extracts are made basic by the addition of solid sodium bicarbonate
  4. extractionextracted with ethyl acetate (4×)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give 8.9 g
  8. customA portion of this material is recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-804c985dc38d4c488e309384c7852386
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04736066

반응 노트

불러오는 중…